Hydrochloric Acid → N-(4-Bromophenyl)propanamide

HRID 1850025Notes

Reaction equation

HRID 1850025 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:18])[CH2:16][CH3:17].Cl>C1(C)C=CC=CC=1>[C:15]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:18])[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 78074-BromoanilineHCID 62324Propionyl chloride

Product 1

HCID 346184N-(4-Bromophenyl)propanamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromoaniline (9.0 g, 52.3 mmol) in PhMe (100 mL) and pyridine (8.5 mL, 110 mmol, 2.0 eq.) was cooled in an ice bath and slowly treated with propionyl chloride (5.5 mL, 63 mmol, 1.2 eq.). After 2 h, the reaction mixture was added to 0.1 M HCl and extracted into EtOAc. Concentration followed by recrystallization of the residue from EtOH/water gave N-propionyl-4-bromoaniline (10.64 g, 89%). [M−H]−=278.1 m/z.

Workup

  1. extractionextracted into EtOAc
  2. concentrationConcentration
  3. customfollowed by recrystallization of the residue from EtOH/water

Sources & evidence

ORD record
ord-81b967ac384146568f6e0c64bbc391b8
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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